| Common Name |
Bethanechol
| Description |
Bethanechol is a synthetic ester structurally and pharmacologically related to acetylcholine. A slowly hydrolyzed muscarinic agonist with no nicotinic effects, bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, cardiac rate changes, and bronchial spasms. [PubChem]
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(2-Hydroxypropyl)trimethylammonium carbamateChEBI
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminiumChEBI
2-Carbamoyloxypropyl-trimethylazaniumChEBI
AmidopropyldimethylbetaineChEBI
Carbamoyl-beta-methylcholineChEBI
Carbamyl-beta-methylcholineChEBI
(2-Hydroxypropyl)trimethylammonium carbamic acidGenerator
Carbamoyl-b-methylcholineGenerator
Carbamoyl-β-methylcholineGenerator
Carbamyl-b-methylcholineGenerator
Carbamyl-β-methylcholineGenerator
BesacholineHMDB
beta-Methyl carbachol chlorideHMDB
Bethaine choline chlorideHMDB
Bethanechol chlorideHMDB
BTCHMDB
Carbamylmethylcholine chlorideHMDB
Chloride, bethanecholMeSH
Organon brand OF bethanechol chlorideMeSH
PMSBethanechol chlorideMeSH
DuvoidMeSH
Hermes, myoMeSH
myo HermesMeSH
MyotonacholMeSH
Roberts brand OF bethanechol chlorideMeSH
Glenwood brand OF bethanechol chlorideMeSH
Hamilton brand OF bethanechol chlorideMeSH
PMS-Bethanechol chlorideMeSH
Pharmascience brand OF bethanechol chlorideMeSH
UrocarbMeSH
BethanecolMeSH
MyocholineMeSH
MyotonineMeSH
PMS Bethanechol chlorideMeSH
| Chemical Formlia |
C7H17N2O2
| Average Molecliar Weight |
161.2221
| Monoisotopic Molecliar Weight |
161.129002798
| IUPAC Name |
1-(trimethylazaniumyl)propan-2-yl carbamate
| Traditional Name |
bethanechol
| CAS Registry Number |
674-38-4
| SMILES |
CC(C[N+](C)(C)C)OC(N)=O
| InChI Identifier |
InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
| InChI Key |
NZUPCNDJBJXXRF-UHFFFAOYSA-O
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic nitrogen compounds
| Sub Class |
Organonitrogen compounds
| Direct Parent |
Tetraalkylammonium salts
| Alternative Parents |
Carboximidic acids and derivatives
Organopnictogen compounds
Organooxygen compounds
Organic salts
Imines
Hydrocarbon derivatives
Amines
Organic cations
| Substituents |
Tetraalkylammonium salt
Carboximidic acid derivative
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic salt
Organooxygen compound
Imine
Amine
Organic cation
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
carbamate ester (CHEBI:3084 )
quaternary ammonium ion (CHEBI:3084 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Muscarinic Agonists
Parasympathomimetics
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point217 – 221 °C (chloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility3.11e-01 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.31 mg/mLALOGPS
logP-2.8ALOGPS
logP-4.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.44 m3·mol-1ChemAxon
Polarizability17.73 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01019
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01019
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Predicted Concentrations |
|
| Biofluid |
Original age |
Original condition |
Blood0-6 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01019
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
2280
| KEGG Compound ID |
C06850
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Bethanechol
| NuGOwiki Link |
HMDB15154
| Metagene Link |
HMDB15154
| METLIN ID |
Not Available
| PubChem Compound |
2370
| PDB ID |
Not Available
| ChEBI ID |
3084
Product: Entecavir
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
Enzymes
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
- Gene Name:
- CHRM2
- Uniprot ID:
- P08172
- Molecular weight:
- 51714.6
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
- Agrawal A, Hila A, Tutuian R, Mainie I, Castell DO: Bethanechol improves smooth muscle function in patients with severe ineffective esophageal motility. J Clin Gastroenterol. 2007 Apr;41(4):366-70. [PubMed:17413603 ]
- Buranakarl C, Kijtawornrat A, Angkanaporn K, Komolvanich S, Bovee KC: Effects of bethanechol on canine urinary bladder smooth muscle function. Res Vet Sci. 2001 Dec;71(3):175-81. [PubMed:11798291 ]
- Cruzblanca H: An M2-like muscarinic receptor enhances a delayed rectifier K+ current in rat sympathetic neurones. Br J Pharmacol. 2006 Oct;149(4):441-9. Epub 2006 Sep 4. [PubMed:16953191 ]
PMID: 15284281
